Triphenylphosphine → tert-butyl [(1S)-2-(4-bromo-3-fluorophenoxy)-1-methylethyl]carbamate
Reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[F:23].O[CH2:25][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:27][C@@H:26]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH3:25])=[CH:18][C:17]=1[F:23]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Diisopropyl azodicarboxylate (1.9 M solution in toluene, 83 mL) was added to a mixture of 4-bromo-3-fluorophenol (25.0 g), tert-butyl [(1S)-2-hydroxy-1-methylethyl]carbamate (25.2 g), triphenylphosphine (41.2 g), and THF (250 mL) dropwise at 0° C. The mixture was stirred at 0° C. for 30 min, and then at room temperature for 3 hr. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (33.7 g) as a pale yellow solid.
Workup
- waitat room temperature for 3 hr
- concentrationThe mixture was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-7c107aa3808547f6bff89b1b4ed307d4
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729102B2
Reaction notes
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